Patent GB-736922-A (GB)
Title: Improvements in photographic colour couplers
IPC: G03C7/36
Filed: 1953-06-26
Abstract: 4 - (a  - 21 - Methoxybenzoyl - a  - chloroacetamido) - 311 - (4111 - tert. - amylphenoxy) - benzanilide is prepared by adding sulphuryl chloride with stirring to 4-(21-methoxybenzoylacetamido) - 311 - (4111 - tert. - amylphenoxy)-benzanilide in dry chloroform. 4-(a -21-Methoxybenzoyl - a  - chloroacetamido) - 211 : 411 - di-tert. - amylphenoxyacetanilide, a  - o - methoxybenzoyl - a  - chloro - 4 - [a  - (2 : 4 - di - tert.-amylphenoxy) - n - butyramido] - acetanilide, a  - chloro - a  - (o - methoxybenzoyl) - 4 - [21-(2111 : 4111 - di - tert. - amylphenoxy) - 51-(3111 : 5111 - dicarbomethoxyphenylcarbamyl]-methoxyacetanilide, and a -(o-methoxybenzoyl)-a  - chloro - 3 - [a  - (21 : 41 - di - tert. - amylphenoxy) - n - butyramido] - acetanilide are similarly prepared. 4 - (21 - Methoxybenzoylacetamido) - 311 - (4111 tert. - amylphenoxy) - benzanilide is prepared by adding m-(p-tert.-amylphenoxy)-benzoyl chloride to a mixture of o-methoxybenzoylacet-4-aminoanilide and sodium acetate-acetic acid solution. 4-(21-Methoxybenzoylacetamido)-211 : 411 - di - tert. - amylphenoxyacetanilide and a  - o - methoxybenzoyl - 4 - [a  - (2 : 4 - di tert.-amylphenoxy) - n - butyramido) - acetanilide are similarly prepared.  o - Methoxybenzoylacet - 4 - aminoanilide is prepared by reducing o-methoxybenzoylacet-4-nitroanilide either with iron powder and acetic acid or with hydrogen over Raney nickel.  o - Methoxybenzoylacet - 4 - nitroanilide is prepared by reacting p-nitroaniline with ethyl o-methoxybenzoylacetate in dry xylene containing anhydrous sodium acetate.  4 - (21 - Methoxybenzoylacetamido) - 211 : 411-di - tert. - amylphenoxyacetanilide is alternatively prepared by refluxing together 4-amino - a  - (21 : 41 - di - tert. - amylphenoxy)-acetanilide and ethyl o-methoxybenzoylacetate in xylene. a  - (o - Methoxybenzoyl) - 4 - [21 - (2111 : 4111-di - tert. - amylphenoxy) - 51 - (3111 : 5111 - dicarbomethoxyphenylcarbamyl) - phenylcarbamyl]-methoxyacetanilide and a -(o-methoxybenzoyl)-3-[a  - (21 : 41 - di - tert. - amylphenoxy) - butyramido]-acetanilide are similarly prepared.  4 - Amino - a  - (21 : 41 - di - tert. - amylphenoxy-acetanilide is prepared by reacting 2 : 4 - di - tert. - amylphenoxyacetyl chloride with p-phenylenediamine.  a  - (2 : 4 - Di - tert. - amylphenoxy) - n - butyryl chloride is prepared by refluxing together di-tert.-amylphenol, sodium hydroxide, and a -bromobutyric acid to give a -(2 : 4-di-tert.-amylphenoxy)-n-butyric acid, and refluxing this acid with thionyl chloride.  a  - (2 : 4 - Di - tert. - amylphenoxy) - 3 - nitrobutyranilide is prepared by reacting a -(2 : 4-di - tert. - amylphenoxy) - butyryl chloride with m-nitroaniline in dioxane containing quinoline.  a  - (2 : 4 - Di - tert. - amylphenoxy) - 3 - aminobutyranilide is prepared by reducing a -(2 : 4-di - tert. - amylphenoxy) - 3 - nitrobutyranilide in ethanol with hydrogen in presence of Raney nickel.  4 - [21 - (211 : 411 - Di - tert. - amylphenoxy-51 - (3111 : 5111 - di - carbomethoxyphenylcarbamyl) - phenylcarbamyl] - methoxyaniline is prepared by reducing 4-[21-(211 : 411-di-tert.-amyl phenoxy) - 51 - (3111 : 5111 - di - carbomethoxy phenylcarbamyl) - phenylcarbamyl] - methoxynitrobenzene with hydrogen in the presence of Raney nickel, sodium carbonate, and ethanol.  4 - [21 - (211 : 411 - Di - tert. - amylphenoxy) 51 - (3111 : 5111 - di - carbomethoxyphenylcarbamyl) - phenylcarbamyl] - methoxynitrobenzene is prepared by heating together 2-(21 : 41-di-tert. - amylphenoxy) - 5 - (311 : 511 - dicarbomethoxyphenylcarbamyl) - aniline, p - nitrophenoxyacetyl chloride, acetic acid, and anhydrous sodium acetate.  2 - (21 : 41 - Di - tert. - amylphenoxy) - 5-(311 : 511 - dicarbomethoxyphenylcarbamyl) - aniline is prepared by reducing with iron and acetic acid 2-(21 : 41-di-tert.-amylphenoxy)-5-(311 : 511 - dicarbomethoxyphenylcarbamyl) - nitrobenzene, itself prepared by heating together 4 - (21 : 41 - di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride, methyl 5-amino-isophthalate, acetic acid, and anhydrous sodium acetate.  4 - (21 : 41 - Di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride is prepared by refluxing with thionyl chloride 4-(21 : 41-di-tert.-amylphenoxy)-3-nitrobenzoic acid, itself prepared by heating together di-tert.-amylphenol, 4-chloro-3-nitrobenzoic acid, and potassium hydroxide.